4-bromo-2-phenylaniline

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Phenyl-4-bromoaniline (564.7 mg, 2.28 mmol) was dissolved in N,N-dimethylformamide (25 mL) and, at room temperature, thereto were added tert-butyl-3-butenoate (582.5 mg, 4.10 mmol), tri-(o-tolyl)phosphine (1.87 g, 6.16 mmol), and diisopropylethylamine (0.78 mL, 4.56 mmol). The reaction mixture was deaerated, palladium acetate (67.4 mg, 0.30 mmol) was added, and the mixture was deaerated again. After stirring at 90° C. overnight, the reaction mixture was filtered through celite and washed with ethyl acetate (120 mL). The organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL), thereafter dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by a silica gel column to obtain tert-butyl (3E)-4-(3-amino-4-phenylphenyl)-3-butenoate (555.8 mg). the reaction mixture was filtered through celite washed with ethyl acetate (120 mL) The organic layer was washed with a saturated aqueous solution of sodium chloride (50 mL) dried over sodium sulfate filtered concentrated under reduced pressure The residue was purified by a silica gel column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Phenyl-4-bromo-N-acetylaniline (7.79 g, 26.85 mmol) was dissolved in ethanol (100 mL), 2 N hydrochloric acid (33.56 mmol, 67.12 mL) was added dropwise under ice bath, and the mixture was heated under reflux overnight. The solution was concentrated under reduced pressure and to the residue were added ethyl acetate (50 mL) and water (40 mL) for extraction. The organic layer was dried over sodium sulfate and, after filtration, concentrated under reduced pressure. The residue was purified by a silica gel column to obtain 2-phenyl-4-bromoaniline (6.58 g). the mixture was heated under reflux overnight The solution was concentrated under reduced pressure and to the residue were added ethyl acetate (50 mL) and water (40 mL) for extraction The organic layer was dried over sodium sulfate after filtration concentrated under reduced pressure The residue was purified by a silica gel column